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Tetrahydrofuran → Tert-butyl[5-{[tert-butyl(dimethyl)silyl]oxy}-2-(4-methylenecyclohexyl)phenoxy]dimethylsilane

HRID 585645
ノート
印刷プレビュー

反応式

HRID 585645 の反応式
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].[Si:7]([O:14][C:15]1[CH:20]=[C:19]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH:18]=[CH:17][C:16]=1C1CCC(=O)CC1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].[Cl-].[NH4+].[CH2:38]1[CH2:42]OC[CH2:39]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:25]([Si:22]([O:21][C:19]1[CH:18]=[CH:17][C:16]([CH:38]2[CH2:42][CH2:3][C:2](=[CH2:5])[CH2:1][CH2:39]2)=[C:15]([O:14][Si:7]([C:10]([CH3:11])([CH3:13])[CH3:12])([CH3:9])[CH3:8])[CH:20]=1)([CH3:24])[CH3:23])([CH3:26])([CH3:27])[CH3:28]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 25517Ammonium ChlorideHCID 223378144-(2,4-Bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexan-1-oneHCID 23665647Potassium tert-butoxide

生成物 1

HCID 17946008Tert-butyl[5-{[tert-butyl(dimethyl)silyl]oxy}-2-(4-methylenecyclohexyl)phenoxy]dimethylsilane収率 68%

試薬・触媒・溶媒 1

HCID 74505Methyltriphenyliphosphonium bromide触媒

実験手順

To a stirred suspension of methyltriphenylphosphonium bromide (329 mg) in anhydrous THF (10 ml) at 0° C. was added potassium tert-butoxide (103 mg) in one portion. After stirring for 30 min, a solution of 4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexanone (200 mg) in THF (5 ml) was added. The reaction mixture was stirred for a further 30 min at 0° C., and saturated aqueous ammonium chloride solution (20 ml) was added. The layers were separated and the aqueous layer extracted with ethyl acetate (3×20 ml). The combined organic phases were washed with brine (20 ml), dried over anhydrous magnesium sulphate, and concentrated in vacuo. Purification via flash column chromatography (SiO2 eluting with diethyl ether:petroleum ether, 1:4 v/v) furnished the title compound as a colourless oil (135 mg, 68%). δH (CDCl3): 0.19 (6H, s), 0.24 (6H, s), 0.97 (9H, s), 1.03 (9H, s), 1.41 (2H, dq), 1.84-1.93 (2H, m), 2.16 (2H, dt), 2.33-2.42 (2H, m), 3.01 (1H, tt), 4.66 (2H, s), 6.29 (1H, dd), 6.40 (1H, dd), 6.94 (1H, d).

後処理

  1. stirringThe reaction mixture was stirred for a further 30 min at 0° C.
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with ethyl acetate (3×20 ml)
  4. washThe combined organic phases were washed with brine (20 ml)
  5. dry with materialdried over anhydrous magnesium sulphate
  6. concentrationconcentrated in vacuo
  7. customPurification via flash column chromatography (SiO2 eluting with diethyl ether:petroleum ether, 1:4 v/v)

出典と根拠

ORDレコード
ord-fbb94498931b4bd2b4abdbac99b87b47
出典データセット
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06933319B2

反応ノート

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